Ben Thompson is the founder of Stratechery, the subscription newsletter that essentially invented the paid independent newsletter model. Writing from Taiwan for over a decade before returning to the US in 2025, he developed Aggregation Theory - the most influential framework for understanding how internet platforms accumulate power - while building a solo business earning $5M+ annually from 40,000+ paying subscribers. Substack's founders literally used him as their pitch-deck inspiration. He also co-hosts three podcasts, including Dithering with John Gruber, where every episode is exactly 15 minutes by design.
Packy McCormick is the founder of Not Boring, a weekly newsletter with 250,000+ subscribers that covers technology, business strategy, and startups through long-form essays. He also runs Not Boring Capital, a solo-GP venture fund with two funds totaling ~$38M invested across 79+ companies. A former investment banker and startup operator, he turned a writing homework assignment into one of the most-read independent tech publications, pioneering a 'media flywheel' model where newsletter content and venture investing reinforce each other.